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Reagent-free intramolecular hydrofunctionalization: a regioselective 6-endo-dig cyclization of o-alkynoylphenols†

Green Chemistry, ISSN: 1463-9270, Vol: 24, Issue: 6, Page: 2376-2384
2022
  • 13
    Citations
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  • 7
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Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    13
    • Citation Indexes
      13
  • Captures
    7

Article Description

Solvent-directed intramolecular hydrofunctionalization of readily available o-alkynoylphenols 1 was successfully achieved under reagent-free conditions. The hydrofunctionalization of 1 occurred by nucleophilic attack on the phenolic oxygen followed by consecutive migration of the phenolic H atom to the alkyne center, eventually affording γ-benzopyranones 2. The phenol O-H group forms intramolecular H-bonds with the carbonyl group, and we predict that these H-bonds can be distorted into their most preferred conformation in the presence of polar solvents. A regioselective 6-endo-dig cyclization seems to be thermodynamically favoured over 5-exo-dig cyclization, as supported by DFT calculations. This strategy is remarkable because it is reagent-free, regioselective, highly atom economical, and highly atom, carbon and reaction mass efficient.

Bibliographic Details

Chanhyun Jung; Siyuan Li; Kwanghee Lee; Mayavan Viji; Heesoon Lee; Soonsil Hyun; Chhabi Lal Chaudhary; Jae Kyung Jung; Kiho Lee; Young Kee Kang

Royal Society of Chemistry (RSC)

Environmental Science

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